After World War I, the U.S. economy grew rapidly, ushering in an era of extravagance and indulgence.
This period, often called the Jazz Age, was marked by lavish spending, debauchery, moral decay, gangster activities, shady dealings, infidelity, and a culture of entertainment at all costs.
At the time, Chicago was essentially a microcosm of American society.
Using a story set in 1920s Chicago to reflect modern reality was sure to resonate with many viewers.
Of course, a large portion of the audience didn't go to the movies to contemplate serious, complex issues—they just wanted to have fun and be entertained.
And Chicago delivered on that front. The film had a gripping plot, two dazzling lead actresses, mesmerizing songs, and captivating dance sequences.
Tom Cruise's portrayal of Billy, dressed in a sleek suit, exuded unparalleled charm.
In short, both male and female audiences could find something they wanted in the film.
Post-production moved along quickly. Chicago required minimal special effects, so most of the work focused on editing and color grading. Gilbert and editor Mehdi spent over half a month working tirelessly, finally completing post-production in early December.
For a commercial film, this was a rather tight schedule, considering that the movie was set to begin its limited release in late December.
However, with a budget of just $20 million and a clear goal of targeting the Oscars, Gilbert wasn't too stressed.
As someone once said, at Gilbert's level, a misstep here and there wasn't a big deal. Besides, it was a musical—if it flopped, it wouldn't be entirely unexpected.
Meanwhile, at Miramax
Harvey and Bob Weinstein were in a meeting with the key figures behind Shakespeare in Love, discussing their awards season strategy.
"Joseph, starting tomorrow, you and Gwyneth will move in together. We need to stir up some dating rumors," Harvey Weinstein said, his massive frame sinking into the couch, which groaned under the strain.
Joseph Fiennes, the film's lead, nodded but voiced a concern. "I'm afraid Gwyneth won't cooperate."
Gwyneth Paltrow hadn't attended the meeting, but Harvey dismissed the worry. "I'll talk to her. If she wants to win the Oscar for Best Actress, she has to play along."
Joseph relaxed. "Alright. I'll cooperate fully with the studio's promotional efforts."
This was a common tactic—actors falling for each other during filming, only to "break up" once the movie's promotional campaign was over.
Most of these relationships were staged, though some did end in real marriage, like Tom Cruise and Nicole Kidman.
Harvey had previously suggested this publicity stunt, but Gwyneth had flatly refused. She simply didn't find Joseph appealing.
However, with Chicago gaining momentum, Harvey had no choice but to persuade Gwyneth to temporarily set aside her misgivings and follow the studio's plan.
Miramax had extensive experience in Oscar campaigns, but Chicago wasn't under their management—even though Miramax was a subsidiary of Disney.
Bob Weinstein voiced his concerns: "I'm worried that Disney will throw its full support behind Chicago, leaving Miramax with no media leverage."
Harvey, however, remained unfazed. "Bob, don't worry. Miramax has always operated independently. It won't be an issue."
What he meant was clear: Disney had never been particularly supportive of them, so they had no reason to expect interference.
That was one of the terms Miramax had secured when Disney acquired them—the guarantee of operational independence, free from corporate meddling.
But Harvey had overlooked one thing. At one point, he had been ambitious about taking a leadership role within Disney, actively involving himself in corporate affairs.
After seeing Michael Ovitz get unceremoniously ousted, however, he abandoned that idea.
Still, once someone inserts themselves into corporate politics, extracting oneself isn't easy.
Sure enough, as if someone had tipped them off, midway through the meeting, Bob Weinstein's phone rang—it was Robert Iger.
"It's Iger," Bob said, glancing at Harvey before answering.
"Mr. Iger, it's Bob speaking… Yes, but… I understand."
Harvey asked, "What's going on?"
Bob's expression darkened. "Iger just told us to put Shakespeare in Love on the back burner. He said all of Disney's awards season efforts should focus on Chicago. Disney won't support our campaign."
"That damn TV guy! He's nothing but Eisner's lapdog—what right does he have to give us orders?" Harvey exploded in anger.
Harvey had always looked down on Robert Iger, calling him the "TV guy" because of his background at ABC. To Harvey, Iger was nothing more than a flashy, talentless executive.
"Then what should we do now?" Bob asked.
"What do you mean?" Harvey was still fuming. "We ignore Disney and stick to our original plan. We're an independent studio, and we don't answer to them."
To be fair, Iger's request was a bit excessive.
Forcing Miramax to step aside just to clear the path for Gilbert was extreme.
Miramax, unlike Touchstone Pictures, didn't have the luxury of profiting from Gilbert's projects every year. Their entire business model revolved around the Oscars—if they abandoned their awards campaign, all their efforts for the year would be wasted. What would happen to their bottom line then?
But from Iger's perspective, Miramax simply wasn't as important as Gilbert. Keeping Gilbert happy was worth more than offending the Weinstein brothers.
That said, Iger's imminent promotion to Disney's president was no secret. If Harvey antagonized him now, things could get messy down the line. This was shaping up to be quite the drama.
Once Chicago was completed, Gilbert took the advice of Warner Bros. executive Doug Walter and arranged for the film to premiere at the Sundance Film Festival.
Sundance was one of the most influential independent film festivals in the U.S., serving as a launching pad for many indie filmmakers to break into the mainstream.
Founded in 1984 by renowned director and actor Robert Redford, the festival was held annually in early January in Park City, Utah.
However, this year was slightly different. In addition to the usual early January event, another festival was scheduled for late December, extending for ten more days into the following January.
For many North American moviegoers, the Sundance Film Festival is as significant as the Toronto International Film Festival held in September.
Compared to North American festivals, European ones like Venice, Cannes, and Berlin hold little appeal for North American audiences. In their eyes, these two domestic festivals matter far more.
Ideally, Gilbert would have preferred Chicago to premiere at the Toronto International Film Festival.
That festival's taste aligns more closely with the Oscars, attracting mostly middle-aged and older audiences—similar to the conservative Academy voters.
However, due to timing constraints, Chicago had to settle for Sundance, which wasn't a bad alternative.
Films that generate buzz at Sundance often perform well in the North American market.
Chicago was featured in the festival's exhibition section. Since Gilbert didn't need to sell distribution rights, he didn't have to cater to film distributors.
The sheer volume of films showcased at Sundance each year is staggering. This year alone, more than 4,000 films were submitted for exhibition before the end of the year.
Even if a festival attendee watched movies nonstop every single day, they wouldn't be able to get through even one-tenth of all the films being shown.
This overwhelming number of submissions was the main reason the festival was extended to 21 days this year—there simply wasn't enough time to fit all the screenings into the original schedule.
As a result, films directed by prominent filmmakers or featuring major stars tend to stand out and draw the most attention.
Without a doubt, Chicago was the festival's most anticipated film, thanks to the combination of Gilbert, Tom Cruise, and Naomi Watts—an exciting trio that heightened expectations.
Aware of Chicago's appeal and knowing exactly what festival audiences wanted to see, the Sundance organizers scheduled Chicago for the opening day of the festival.
To promote the film, Gilbert and the three lead actors attended the premiere screening, marking the first major sensation of the Sundance Film Festival.
The screening was held in a large makeshift tent theater that could accommodate nearly a thousand viewers.
Although it was the middle of winter and snowflakes were falling outside, the cold weather did not dampen the audience's enthusiasm. Gilbert's collaboration with Tom Cruise generated immense anticipation, and everyone wanted to experience the film firsthand.
Chicago's outstanding performance won over even the most discerning festival audiences.
Sundance audiences are very different from those at the Toronto International Film Festival.
In Toronto, regardless of a film's quality, audiences will always offer polite applause.
Sundance audiences, on the other hand, are much more critical. If a film doesn't impress them, they won't bother clapping or cheering.
This selectiveness is one of the reasons why Sundance has become a major launchpad for independent filmmakers entering the mainstream film industry. After all, if a film can win over Sundance audiences, it has a strong chance of succeeding in the broader market.
On this demanding stage, Chicago unquestionably captivated all viewers.
As word-of-mouth spread, tickets for Chicago's subsequent screenings became nearly impossible to obtain, making it the most popular and highly anticipated film of the Sundance Film Festival.
Unsurprisingly, Chicago was selected for the competition section, though the awards ceremony was still some time away.
The Chicago team stayed at the festival for only two days to generate buzz, planning to return again for the awards ceremony.
While wandering around the festival, Gilbert happened to notice someone—a director he had greatly admired in his past life.
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